In order to gain a bit of perspective about Charlton Hall, we need to take a look back at the first owner's father, David Dows, Sr. He was born a farmer's son in 1814. When he left his father's home in 1828 to work in a dry goods store, there were fewer than 20 miles of railroad tracks in the country. The nation was poised for expansion and railroads played a major role, not just by physically opening up access to the West, but economically as well. Dows was heavily involved in the growth of the railroad and all of the profits that could be reaped from previously untapped markets.

Dows was also a prosperous grain merchant who built grain elevators in the northwestern and western grain-producing states and he was involved in the development of the rail lines to reach the growers. Shipments of grain were also supplied to continental markets. In 1846, Dows found himself in possession of a glut of grain when demand dropped. However, a sudden surge of demand arrived the following year in the form of the Irish famine. The price of grain soared and enormous profits were reaped.

When the U.S. Civil War broke out in 1860, the government needed a way to provision the troops. The Commissary-General had difficulties purchasing supplies in some of the then-western cities such as Cincinnati. When the government approached the market, the prices were fixed at a high rate. However, as a private citizen, Dows was able to purchase the necessary supplies and deliver thousands of packages of provisions to the Commissary Department.

As the country shifted away from the gold standard to guarantee the value of its currency, and a new, government-based banking system was evolving in the wake of the war, Dows was one of the original investors in the Fourth National Bank. He was also a founding member of several other banking and financial institutions.

In 1872, Dows was also involved in the funding of the New York Elevated Railroad Company, one of the first rapid transit systems for the city. By the time he died in 1890, he had not only amassed several fortunes, but he had also helped to shape the nation in terms of the expansion the railroad into untapped western grain markets as well as being a part of creating banking institutions that still stand today. Being born into a time of great opportunity with the ability to capitalize upon it made David Dows Sr. a memorable man. His son, nicknamed "Big Dave" would also go on to make his mark in the business world, but he had very large shoes to try to fill.